title: Effects of methylation and ring size on mutagenicity of cyclic nitrosamines in Drosophila melanogaster.
abstract: The mutagenic activity of 7 nitrosopiperazines, 2 nitropyrrolidines, and 3 nitrosomorpholines was examined in the X-linked recessive-lethal assay of Drosophila melanogaster. Mutagenicity is also reported for a series of cyclic nitrosamines that differ in structure only in the number of carbon atoms in the ring. Of the 18 compounds tested, 6 (nitrosopiperazine; 2,3,5,6-tetramethyldinitrosopiperazine; nitrosoproline; 2,5-dimethylnitrosopyrrolidine; nitrosothiomorpholine; and nitrosooctamethyleneimine) were nonmutagenic. As we reported earlier in investigations with the nitrosopiperidines, substitutions with methyl groups at all of the alpha-carbon atoms reduce or eliminate the mutagenic activity of dinitrosopiperazine and nitrosopyrrolidine.
mesh_terms: D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D004331:Drosophila melanogaster / Q000187:drug effects / Q000235:genetics*; D005804:Genes, Lethal / Q000187:drug effects; D005808:Genes, Recessive / Q000187:drug effects; D008297:Male; D008745:Methylation; D009152:Mutagenicity Tests; D009154:Mutation; D009602:Nitrosamines / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D009602:Nitrosamines